James Montgomery Flagg's portrait of writer Ring Lardner depicts an enigmatic "professional humorist who sometimes smiled but never laughed." Lardner's fiction was admired for its command of colloquial language and its non-idealized characters. "I try to write about people as real as possible," he once wrote. Lardner's You Know Me, Al (1916), featuring the letters of a fictional rookie ballplayer, established the author's reputation and inspired a comic strip. This drawing appeared in a 1922 advertisement for the strip and was later published in a collection of Flagg's celebrity portraits. Flagg drew Lardner from life, deftly documenting his thin, downturned lips, heavy-lidded "owl eyes," and angular nose and chin. The artist, best known for his Uncle Sam "I Want You" recruiting poster, succeeds in capturing that "mask over his emotions," which disguised but did not diminish Lardner's keen wit.